Edward Hopper maintained a lifelong interest in nautical themes, a passion that began in his early life growing up in the village of Nyack, New York, once known for its port and former shipbuilding industry on the west bank of the Hudson River.

[2] He would often bicycle from his home to the end of Van Houten Street to watch boats being built and launched at the shipyards.

The Mansard Roof stole the show, received critical acclaim, and was purchased by the museum, marking Hopper's second major sale.

Hopper produced dozens of paintings focusing on seascapes, maritime landscapes, rivers, bridges, bay views from houses,[2] and the architecture of lighthouses and coastal towns in New England.

[6] 1925 was a major turning point for Hopper, demarcating the transition from his early period to his middle or mature style as an artist.

[7] The year began with the death of fellow Ashcan artist George Bellows (1882–1925), whose passing evoked a rare emotional response from Hopper.

[8] Hopper began selling his first works to museums, with the Pennsylvania Academy of the Fine Arts purchasing Apartment Houses (1923) in March.

[6] The problem had increased to such a point that the United States Attorney General made an announcement in February publicly declaring the illegal actions of foreign ships helping the bootlegging industry, who waited off the coast for small boats to arrive and transfer the cargo to their holds.

[9] According to art historian Gail Levin, these small boats, often known as "rummies", were used as the basis for the scene depicted in The Bootleggers.

"[10] Art dealer John Clancy, who was managing the Rehn Gallery when the painting was sold in 1956, explained that the imagery depicted in The Bootleggers was based on a mixture of different scenes; it did not represent an actual place.

His interest in the former was partly due to a sense of nationalism that was flourishing at the time, but also to having visited Europe, allowing him to self-reflect and recognize the American style he had been surrounded with from the beginning.

Shortly after its creation, the Brooklyn Museum featured it in the Paintings in Oil by American and European Artists exhibition, which ran from late November 1925 to early January 1926.

By the end of that month, it was displayed again alongside Hopper's prints from late January to mid-February 1926 in the Exhibition of Tri-National Art, which toured Paris, London, New York City, and Germany.

[8] Early that next year, the painting was acquired from the Rehn Gallery by Charles E. Buckley for the Currier Museum of Art.